#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/29/4022950.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022950
loop_
_publ_author_name
'Jeremy P. Scott'
'David R. Lieberman'
'Olivier M. Beureux'
'Karel M. J. Brands'
'Antony J. Davies'
'Andrew W. Gibson'
'Deborah C. Hammond'
'Chris J. McWilliams'
'Gavin W. Stewart'
'Robert D. Wilson'
'Ulf-H. Dolling'
_publ_section_title
;
 A Practical Synthesis of a γ-Secretase Inhibitor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4149
_journal_page_last               4155
_journal_paper_doi               10.1021/jo070407n
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C18 H15 Cl F2 O3 S'
_chemical_formula_sum            'C18 H15 Cl F2 O3 S'
_chemical_formula_weight         384.81
_chemical_name_common            jrc0831n
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.450(10)
_cell_length_b                   10.490(7)
_cell_length_c                   10.828(7)
_cell_measurement_reflns_used    3268
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.43
_cell_measurement_theta_min      2.35
_cell_volume                     1755(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1182
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13312
_diffrn_reflns_theta_full        26.47
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                2707
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070407nsi20070228_061757.cif
_cod_data_source_block           jrc0831n
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     p_2c_-2ac
_cod_database_code               4022950
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.74403(11) 0.13457(13) 0.00974(19) 0.1253(6) Uani 1 1 d .
C1 C 0.8086(3) 0.2567(4) 0.0673(5) 0.0730(12) Uani 1 1 d .
C2 C 0.7752(3) 0.3364(4) 0.1558(5) 0.0754(12) Uani 1 1 d .
H2 H 0.7191 0.3246 0.1849 0.091 Uiso 1 1 calc R
C3 C 0.8256(2) 0.4342(3) 0.2012(4) 0.0580(9) Uani 1 1 d .
H3 H 0.8035 0.4895 0.2605 0.070 Uiso 1 1 calc R
C4 C 0.9093(2) 0.4497(3) 0.1580(3) 0.0446(8) Uani 1 1 d .
S1 S 0.97363(4) 0.57511(8) 0.21245(9) 0.0432(2) Uani 1 1 d .
O1 O 0.93949(15) 0.6123(3) 0.3313(2) 0.0569(6) Uani 1 1 d .
O2 O 1.06255(13) 0.5385(2) 0.2039(3) 0.0616(6) Uani 1 1 d .
C5 C 0.9421(2) 0.3678(3) 0.0697(3) 0.0539(9) Uani 1 1 d .
H5 H 0.9982 0.3783 0.0402 0.065 Uiso 1 1 calc R
C6 C 0.8906(3) 0.2703(3) 0.0258(4) 0.0650(11) Uani 1 1 d .
H6 H 0.9124 0.2138 -0.0326 0.078 Uiso 1 1 calc R
C7 C 0.8017(2) 0.6814(3) 0.0204(3) 0.0493(8) Uani 1 1 d .
F2 F 0.83188(15) 0.6026(2) -0.0688(2) 0.0734(7) Uani 1 1 d .
C8 C 0.7137(2) 0.7021(4) 0.0225(4) 0.0641(10) Uani 1 1 d .
H8 H 0.6783 0.6627 -0.0355 0.077 Uiso 1 1 calc R
C9 C 0.6788(2) 0.7795(4) 0.1091(4) 0.0678(11) Uani 1 1 d .
H9 H 0.6195 0.7951 0.1113 0.081 Uiso 1 1 calc R
C10 C 0.7337(2) 0.8341(3) 0.1935(4) 0.0571(9) Uani 1 1 d .
F1 F 0.69915(14) 0.9129(2) 0.2800(3) 0.0892(8) Uani 1 1 d .
C11 C 0.82032(19) 0.8144(3) 0.1923(3) 0.0450(8) Uani 1 1 d .
H11 H 0.8547 0.8544 0.2511 0.054 Uiso 1 1 calc R
C12 C 0.85894(18) 0.7355(3) 0.1048(3) 0.0379(7) Uani 1 1 d .
C13 C 0.95664(18) 0.7101(3) 0.1080(3) 0.0384(7) Uani 1 1 d .
C14 C 1.0002(2) 0.6822(3) -0.0167(3) 0.0483(8) Uani 1 1 d .
H14A H 1.0605 0.6601 -0.0033 0.058 Uiso 1 1 calc R
H14B H 0.9720 0.6101 -0.0558 0.058 Uiso 1 1 calc R
C15 C 1.0075(2) 0.8202(3) 0.1681(3) 0.0481(8) Uani 1 1 d .
H15A H 0.9840 0.8378 0.2494 0.058 Uiso 1 1 calc R
H15B H 1.0676 0.7955 0.1779 0.058 Uiso 1 1 calc R
C16 C 0.9947(2) 0.7986(4) -0.1019(4) 0.0616(10) Uani 1 1 d .
H16A H 1.0302 0.7830 -0.1742 0.074 Uiso 1 1 calc R
H16B H 0.9354 0.8080 -0.1295 0.074 Uiso 1 1 calc R
C17 C 1.0020(3) 0.9392(4) 0.0891(5) 0.0659(10) Uani 1 1 d .
H17A H 0.9438 0.9733 0.0953 0.079 Uiso 1 1 calc R
H17B H 1.0412 1.0025 0.1228 0.079 Uiso 1 1 calc R
C18 C 1.0230(2) 0.9209(4) -0.0440(4) 0.0632(11) Uani 1 1 d .
O3 O 1.0590(2) 1.0036(3) -0.1016(4) 0.1016(12) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 121.4(4)
C6 C1 Cl1 119.7(3)
C2 C1 Cl1 118.9(3)
C1 C2 C3 119.3(4)
C1 C2 H2 120.3
C3 C2 H2 120.3
C2 C3 C4 119.6(4)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 120.2(3)
C5 C4 S1 119.5(3)
C3 C4 S1 120.3(3)
O2 S1 O1 118.76(16)
O2 S1 C4 108.75(16)
O1 S1 C4 107.22(16)
O2 S1 C13 107.78(14)
O1 S1 C13 106.79(15)
C4 S1 C13 106.97(15)
C6 C5 C4 119.2(3)
C6 C5 H5 120.4
C4 C5 H5 120.4
C1 C6 C5 120.2(4)
C1 C6 H6 119.9
C5 C6 H6 119.9
F2 C7 C8 116.6(3)
F2 C7 C12 119.9(3)
C8 C7 C12 123.5(3)
C9 C8 C7 120.0(3)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 117.8(3)
C8 C9 H9 121.1
C10 C9 H9 121.1
C11 C10 F1 119.2(3)
C11 C10 C9 122.7(4)
F1 C10 C9 118.1(3)
C10 C11 C12 121.4(3)
C10 C11 H11 119.3
C12 C11 H11 119.3
C7 C12 C11 114.6(3)
C7 C12 C13 124.7(3)
C11 C12 C13 120.6(3)
C12 C13 C14 116.4(3)
C12 C13 C15 112.4(2)
C14 C13 C15 106.9(3)
C12 C13 S1 106.9(2)
C14 C13 S1 109.4(2)
C15 C13 S1 104.2(2)
C16 C14 C13 110.6(3)
C16 C14 H14A 109.5
C13 C14 H14A 109.5
C16 C14 H14B 109.5
C13 C14 H14B 109.5
H14A C14 H14B 108.1
C17 C15 C13 110.5(3)
C17 C15 H15A 109.5
C13 C15 H15A 109.5
C17 C15 H15B 109.5
C13 C15 H15B 109.5
H15A C15 H15B 108.1
C18 C16 C14 114.6(3)
C18 C16 H16A 108.6
C14 C16 H16A 108.6
C18 C16 H16B 108.6
C14 C16 H16B 108.6
H16A C16 H16B 107.6
C18 C17 C15 115.3(4)
C18 C17 H17A 108.4
C15 C17 H17A 108.4
C18 C17 H17B 108.4
C15 C17 H17B 108.4
H17A C17 H17B 107.5
O3 C18 C17 120.6(4)
O3 C18 C16 122.4(5)
C17 C18 C16 116.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.740(4)
C1 C6 1.352(6)
C1 C2 1.373(6)
C2 C3 1.378(5)
C2 H2 0.9300
C3 C4 1.385(4)
C3 H3 0.9300
C4 C5 1.381(5)
C4 S1 1.751(4)
S1 O2 1.430(2)
S1 O1 1.445(3)
S1 C13 1.831(3)
C5 C6 1.381(5)
C5 H5 0.9300
C6 H6 0.9300
C7 F2 1.355(4)
C7 C8 1.377(5)
C7 C12 1.392(4)
C8 C9 1.352(6)
C8 H8 0.9300
C9 C10 1.373(6)
C9 H9 0.9300
C10 C11 1.355(4)
C10 F1 1.357(4)
C11 C12 1.392(4)
C11 H11 0.9300
C12 C13 1.533(4)
C13 C14 1.537(5)
C13 C15 1.541(4)
C14 C16 1.533(5)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C17 1.516(6)
C15 H15A 0.9700
C15 H15B 0.9700
C16 C18 1.493(6)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.490(7)
C17 H17A 0.9700
C17 H17B 0.9700
C18 O3 1.204(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8605565
